A Scalable Route to the SMO Receptor Antagonist SEN826: Benzimidazole Synthesis via Enhanced in Situ Formation of the Bisulfite–Aldehyde Complex

Autor:	Paul H. Wiedenau, Matteo Betti, Salvatore Sanna Coccone, Eva Genesio, Guido Marconi
Rok vydání:	2014
Předmět:	chemistry.chemical_classification In situ Benzimidazole medicine.drug_class Stereochemistry Organic Chemistry Receptor antagonist Aldehyde Combinatorial chemistry Bisulfite chemistry.chemical_compound chemistry Scalability medicine Molecule Physical and Theoretical Chemistry
Zdroj:	Organic Process Research & Development. 18:699-708
ISSN:	1520-586X 1083-6160
DOI:	10.1021/op4002092
Popis:	A practical and scalable route to the SMO antagonist SEN826 1 is described herein, including the discussion of an alternative approach to the synthesis of the target molecule. The optimized route consists of five chemical steps. A new and efficient access to the key intermediate 6 via the bisulfite–aldehyde complex was developed, significantly enhancing the yields and reducing costs. As a result, a synthetic procedure for preparation of multihundred gram quantities of the final product has been developed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::d348b1c5f978bdd85c3fef7d3001d680 https://doi.org/10.1021/op4002092 Zobrazit plný text záznamu